To say the best has been saved for last would be pretty dismissive of the past four volumes. Nonetheless, I’ve saved some of my personal favorites for this final installment: Classics Old and New.

If you’re listening on Apple Music, I think you have the good fortune of starting off with a classic opener from Rockapella. Their original Christmas album is terrific all on its own. 

Another album that stands out from start to finish is CeeLo Green’s Christmas album, ​CeeLo’s Magic Moment. (When I first saw that CeeLo Green had a Christmas album I was enormously skeptical and now I  recommend it to anyone and everyone who will listen—and some who won’t...) His recording of “What Christmas Means to Me” is hands-down the best version. Period. Full stop. (I will fight you!)

Continuing in the old classics vein is Mariah’s legendary “All I Want for Christmas Is You” and Vince Guaraldi Trio’s “Christmas Time Is Here (Instrumental)”. (The kids’ voices are adorable… when you’re watching the movie. Incidentally, the words were written by the film’s director out of necessity. It was too late in production for them to find a professional lyricist!).

There are some standard bearers of yore—the self-assured baritone charm of Robert Goulet with “Sleigh Ride”, Tony Bennett’s live performance of “I’ll Be Home for Christmas”, and Nat King Cole’s “Deck the Halls”, the Percy Faith Orchestra, Herb Alpert, and the Carpenters.

You’ll also find some modern vocal virtuosos—Michael Bublé (bridging the old and the new in his own way), Christina Aguilera, Kacey Musgraves, and Celine Dion. (Singers know that “O Holy Night” is a heck of a song, and she sings the heck out of it.)

When I think of Christmas music, Mannheim Steamroller is one of the first sounds that comes to mind. Naturally, a few of their songs appear here, as well as the Trans-Siberian Orchestra’s dramatic rendering of “Carol of the Bells”, now a classic in itself.

Of the many trivial musical “injustices” out there, the limited acceptance of a cappella music is one of my pet peeves. That groups like Straight No Chaser and Pentatonix are more popular during Christmas is definitely what makes this the most wonderful time of the year. But come on, people! Listen to Pitch Slapped wail on “Joy to the World” and tell me that’s not amazing! And you truly have not heard “You’re a Mean One, Mr. Grinch” until you’ve heard Rockapella sing it. Seriously. Brace yourself.

Broadway luminaries are also quite capable of making the season bright. Linda Eder, Idina Menzel, Leslie Odom, Jr., each with their own bit of magic. One of my favorite Carols for a Cure recordings remains the cast of Mamma Mia! taking on “O Holy Night” (they too sing the heck out of it, but in a very different way).

Unsurprisingly, my parents were the ones who first got me turned onto Christmas music. A stack of LPs, turned into a pile of tapes, which grew into a basket of CDs that we looked forward to pulling out of the attic every year. One of their favorite holiday albums is the Manhattan Transfer’s first Christmas album, a dazzlingly jazzy treasury of tunes. I thought it only appropriate to end the playlist with one of our favorite cuts. The final moments of their Santa Claus medley sums up how I feel about this genre and this time of year.

(And yes, if you want to find out what that is, you’ll just have to listen…)

Oh, where to begin? Why are these “stocking surprise” tracks? Firstly, my ear demands alliteration. Secondly, and more importantly, there are some pretty surprising teams, arrangements and sounds in this mix.

Starting with Scott Bradlee’s mile-a-minute piano in Sleigh Ride, with a stylistic tour-de-force vocal arrangement of “O Come, All Ye Faithful” from Pentatonix. (Fans of key changes and “acappella-sounding sections with acapella songs” will not be disappointed).

If you happen to remember, “All For You” by Sister Hazel… you are at least as old as I (and you have my sympathy) but they’re here with an acoustic rendering of “Have Yourself a Merry Little Christmas”.

One of the most surprising of the bunch is CeeLo Green’s collaboration with the Muppets. Devotees of Jim Henson’s genius will appreciate the new life breathed into “Mahna Mahna” awakened and dusted off just for the holidays. (And yes, Statler and Waldorf have something to say about the whole affair at the end). The original Brothers Snark are truly classics in and of themselves.

Let’s see, what else? A flamenco-flavored "Carol of the Bells”, a mambo-mix of “Rudolph”, and a precise but gritty blues rendition of “Jingle Bells” from James Taylor. (Those bells have never jingled so hard all the way to wherever they’re going.)

Then a few unexpected pairings worth listening to: Barenaked Ladies and Sarah McLachlan (what?), Ingrid Michaelson with Leslie Odom Jr. (hmm…), tobyMac featuring Owl City (the hardest take on the First Noel you’ve heard), and then back to BNL with… Michael Bublé? (released long before the working conditions of Amazon warehouse personnel were exposed, this hits a little different now…) Later Stephen Colbert and Jon Stewart compare and contrast Christmas and Hanukkah. Perhaps the best combination of voices and sounds comes with the last cut—Pentatonix and the Manhattan Transfer taking on “White Christmas” … It is easily one of the best technical arrangements out there, jumping all over the stylistic map and featuring the unique strengths of each group, neatly complemented by the other ensembles vocals.

It’s all here, folks. Mariah providing vocals for a “whistle tone" Nutcracker? Check. Country western cats ambling through “Silent Night”? Check. A funky acappella reimagining of the night before Christmas poem? Check.

Do not let the smooth sound of Barry Manilow’s recording of “River” deceive you—while not as raw as the original, there is a poignance and honesty to it that can only be conveyed by the man who sang yearningly of “Mandy" decades ago.

Perhaps most surprising is Straight No Chaser’s choice to include Counting Crows’s “A Long December” as part of their most recent holiday album. Even more surprising? They actually pull it off. I’ve sat at many a piano and played this song literally hundreds of times over the years and not once did I ever think of it as a Christmas song, but it definitely works. Each listen evokes a sense of wonder and delight in their successful “seasonalization” of a 90s classic. The wistful ballad is made even more melancholy when adorned with the trimmings and trappings of holiday motifs. 

Enjoy these stocking surprises!

What makes a holiday classic? Heck if I know! Regardless, here are some Christmas songs I rarely—if ever—see covered by other artists on seasonal albums. 

“Snow Globe” by Matt Wertz bounces with so much Christmas spirit, it's like listening to a mug of hot chocolate. I’ve loved this song since I first stumbled across it years ago and it’s also part of my “Morning after Thanksgiving” playlist to welcome the season.

Still waiting to find out what Pasesk & Paul can’t do. (Hint: It’s not write a Christmas song, because they wrote a whole musical, plus this second gem, “Count on Christmas” recorded by Bebe Rexha). Buoyant in a different way, but still sparkling like a star a-top a tree.

Sia is brave. When I first saw she had a Christmas album, I wondered what sort of new spin she was going to put on the old songs everyone chooses. My skepticism was thankfully and thoroughly dashed with a whole album of originals, including “Candy Cane Lane”.

Other comments about stand-out songs (among many outstanding Christmas originals):

Kristin Chenoweth’s “Home on Christmas Day” is beautiful, but was clearly written for someone like Josh Groban. Listen to it and you’ll see what I mean.

“Indiana Christmas” by Straight No Chaser will never not get me choked up:
“And I remember those who are gone / Looking down on my home from above. Deep in December is where I belong / Sharing the days with the ones who I love.” I mean, come on.

Jason Gray’s “Christmas Is Coming” is a compelling anthem that reminds us of the reason for the season without sacrificing the need to be catchy.

Not all songs are new — Surprisingly enough, “Oh Santa!” is a decade old; it’s just been resurrected by Mariah Carey with a little help from modern powerhouses Jennifer Hudson and Ariana Grande. Incidentally, ​Mariah Carey’s Magical Christmas Special is a pleasant waste of time, so don’t. It’s still likely better than the Grinch on NBC.  ?  Diane Birch’s “Gee Whiz It’s Christmas” was actually written in the late 1950s. No wonder the retro sound is so authentic, right?

Due to licensing and streaming balderdash, I do not know if the playlists will include “I Can See the Light” but I really encourage everyone to check it out. Featuring Anthony Ramos and the cast of Hamilton, “I Can See the Light” was included in 2016’s Carols for a Cure collection of Christmas songs recorded by shows currently running on Broadway, to raise money for AIDS research. I don’t want to overpromise it as a “transformative” song, but it certainly can remind us why we should remain open to a higher power, whatever its name. Even non-believers can believe in Hope.

Last but not least, “Ribbons and Bows” by Kacey Musgraves. Wow... just, wow. Simple, but still classic Kacey—catchy and elegant. Like a point guard faking right and going left, my favorite lyrical phrase, “expensive rings and diamond things” always makes me chuckle.  

Expected, and yet not. Maybe that’s what makes a holiday classic. It’s a good start, anyway.

As always, plenty of David Arkenstone to be found on this mix, but many different styles—you would think that with so many Christmas albums out there, he’d start to repeat himself. While there are similarities, each album has a unique sound. Who knew that the guy responsible for the soaring “Deck the Halls” from Volume 1, was also capable of chill lounge version of “O Come All Ye Faithful” that—against all heavenly reason—actually works.

I didn’t think there could be a good, non-frantic recording of “All I Want for Christmas Is You” until I stumbled across Michael Forster’s recording several years ago. I tried to think of other strong openers for the playlist, but I chose this because it serves as a little dare—daring you, the listener, to dismiss such a gorgeous rendition just because it departs so drastically from the Mariah version that we all know and love.

You’ll notice that like David Arkenstone’s ubiquity, there are quite a few tracks from Gary Prim and David Combs. Growing up, we would listen to Gary Prim cassette tapes to fall asleep. His simple, elegant version of “God Rest Ye Gentlemen” brings me almost immediate tranquility as that is what I frequently hear as I put my head on my pillow to sleep.

Kaskade almost didn’t make the cut. “Christmas Is Here” is not a mislabeled Peanuts ballad, but rather a haunting, club version of "Carol of the Bells” … Whatever creepy vibes the singers voice gives off are not sinister enough to keep it from finding its relaxing, albeit interesting, groove in the mix.